| Connecticut Yankee Council, Inc., Boy Scouts of America | Other Services (except Public Administration) | $288,500 | $290,263 | 18 | N/A |  AI Deep Dive |
| Coastline Insulation, LLC | Construction | $285,842 | $289,413 | 11 | <$5M | AI Deep Dive |
| Rick's Plumbing Service INC | Construction | $282,115 | $285,525 | 28 | $8.9M | AI Deep Dive |
| B & a Company Inc. | Manufacturing | $277,643 | $280,473 | 16 | <$5M | AI Deep Dive |
| B & a Company, Inc. | Manufacturing | $277,642 | $280,758 | 17 | <$5M | AI Deep Dive |
| Milford Brewing Company LLC | Manufacturing | $274,500 | $276,364 | 63 | $22.2M | AI Deep Dive |
| The Idea Company, LLC | Professional, Scientific, and Technical Services | $273,000 | $275,977 | 18 | <$5M | AI Deep Dive |
| Milford Podiatry Associates, P.c. | Health Care and Social Assistance | $271,908 | $273,630 | 23 | <$5M | AI Deep Dive |
| Milford Podiatry Associates PC | Health Care and Social Assistance | $271,907 | $274,301 | 23 | <$5M | AI Deep Dive |
| Power and Network Solutions LLC | Construction | $270,000 | $271,176 | 9 | <$5M | AI Deep Dive |
| Slm & Jiml, LLC | Health Care and Social Assistance | $269,800 | $272,653 | 45 | $7.3M | AI Deep Dive |
| Charter Oak Environmental, LLC | Administrative and Support and Waste Management | $269,695 | $274,108 | 18 | <$5M | AI Deep Dive |
| Bbi Technologies Inc. | Real Estate and Rental and Leasing | $267,550 | $269,482 | 16 | $7.2M | AI Deep Dive |
| Bonfire Grille LLC | Accommodation and Food Services | $266,599 | $268,228 | 7 | <$5M | AI Deep Dive |
| Anela Inc. | Accommodation and Food Services | $264,586 | $266,592 | 30 | $5.3M | AI Deep Dive |
| Alcat Incorporated | Manufacturing | $263,645 | $266,318 | 21 | $5.1M | AI Deep Dive |
| Climate Partners LLC | Construction | $262,267 | $265,057 | 20 | $6.3M | AI Deep Dive |
| Ahip Ct Milford Enterprises LLC | Accommodation and Food Services | $261,488 | $265,027 | 59 | $18.4M | AI Deep Dive |
| Perrys and Tonys INC DBA Bridgeport Flyer Diner0 | Accommodation and Food Services | $261,243 | $263,576 | 32 | $5.7M | AI Deep Dive |
| Athenian Diner of Middletown INC | Accommodation and Food Services | $258,580 | $260,401 | 24 | <$5M | AI Deep Dive |
| Kasteli L L C | Accommodation and Food Services | $256,858 | $259,307 | 40 | $7.1M | AI Deep Dive |
| Whale Precision Manufacturing Inc. | Manufacturing | $252,100 | $253,963 | 15 | <$5M | AI Deep Dive |
| Maintenance Technologies | Professional, Scientific, and Technical Services | $251,065 | $252,883 | 13 | <$5M | AI Deep Dive |
| Duck Pond Day Care INC | Health Care and Social Assistance | $249,170 | $252,319 | 35 | $5.7M | AI Deep Dive |
| Whale Precision Manufacturing Inc. | Manufacturing | $247,898 | $249,798 | 15 | <$5M | AI Deep Dive |